Cesium carbonate → HCID 67316628, compound

HRID 503551Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12][CH3:13])=[CH:7]2.[C:14]1([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([OH:37])=[N:35][CH:36]=3)=[N:22][N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([O:37][C:34]3[N:35]=[CH:36][C:31]([NH:30][C:23]4[C:24]5[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:20]([C:14]5[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=5)=[N:21][N:22]=4)=[CH:32][CH:33]=3)=[CH:3][CH:4]=[N:5]2)=[N:10][CH:9]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A pyrex reaction tube was charged with 8-chloro-3-methoxy-1,5-naphthyridine (50 mg, 0.26 mmol), 5-(4-phenylphthalazin-1-ylamino)pyridin-2-ol (80 mg, 0.26 mmol), cesium carbonate (249 mg, 0.76 mmol) and DMSO (2 mL). The tube was sealed and the reaction mixture was heated to 130° C. After 3.5 h, an aliquot was analyzed by LCMS, and the desired product was determined to be the major peak. The reaction mixture was diluted with DMSO and purified by Gilson HPLC {5-65% (0.1% TFA in CH3CN) in H2O over 20 min}. The product-containing fractions were combined, basified by addition of aq. NaHCO3 and extracted with DCM. The organic portion was dried with Na2SO4, filtered, and concentrated to afford material that was further purified by silica gel chromatography, 90/10/1 CH2Cl2/MeOH/NH4OH. This provided N-(6-(7-methoxy-1,5-naphthyridin-4-yloxy)pyridin-3-yl)-4-phenylphthalazin-1-amine as pure material. MS [M+H][email protected] minutes. Calc'd for C28H20N6O2: 472.5.

Workup

customThe tube was sealed

Sources & evidence

ORD record: ord-6ae0a6b1fed544e7bcc1c2dd7174576d
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776857B2

Reaction notes

Loading…